Nobody can skewer young love with the gauche emotion, mordant wit or rude detail of Conor Oberst. The Bright Eyes maestro is only twenty-four, but he’s broken a career’s worth of hearts, strumming his acoustic guitar and chronicling his romantic torments in indie-rock gems such as “Going for the Gold.” He commands a cult of hot, sullen Conorites who would gladly crawl through broken glass to lick his plectrum. And though he blew up nationwide with his previous album, 2002’s Lifted, and is a veteran of both the Vote for Change Tour and The O.C., he still sticks to the tiny indie label he helped establish in 1993, when he was just a thirteen-year-old Omaha, Nebraska, kid peddling his home demos. Respect!

His two new albums are completely different animals. I’m Wide Awake, It’s Morning is a masterpiece of country-flavored heartland angst, plowing the musical ground between The Freewheelin’ Bob Dylan and the Cure’s Seventeen Seconds. Digital Ash in a Digital Urn is a more self-conscious studio experiment, with Kid A-inspired synth diddles. Any mortal songwriter would get slaughtered attempting the emotional excesses of these tunes; sometimes it takes four or five minutes to tell whether it’s a good one or not. But Oberst is brilliant at going too far, riding the subways with grievous angels and lost souls even more screwed up than he is. He really puts on the chill in Wide Awake‘s “Lua,” an acoustic ballad about doing drugs all night with a desperate lover with a heavy heart (“So many men stronger than me/Have thrown their backs out trying to lift it”). By morning, they can’t even recognize each other. You’d have to go back to Guns n’ Roses’ “Night Train” for a more harrowing chemical romance, especially when Oberst croaks, “Me, I’m not a gamble/You can count on me to split.”

Wide Awake has the loose, spontaneous feel of a Bright Eyes show, where Oberst basically just plays with whichever musical friends feel like showing up. Emmylou Harris harmonizes on three tracks — if people are going to keep comparing you to Gram Parsons, you may as well go all the way — though she’s more of a symbolic casting coup than a musical presence. But it comes down to the songs, and these are the most intense he’s ever written, one instant classic after another. Oberst burns through throwaway couplets (“The moon’s laying low in the sky/Forcing everything metal to shine”) and full-blown New York love songs such as “Train Under Water.” Best of all, there’s the longtime live fave “First Day of My Life,” a rapturous ditty with the sharpest and simplest lines he’s ever sung about long-term romance: “I’d rather be working for a paycheck/ Than waiting to win the lottery.”

The superbly titled Digital Ash is strangely backloaded: The good songs don’t start kicking in until about halfway through, after many synth glitches and botched break beats. But once it gets going, it’s phenomenal, with OMD-style guitar and keyboard hooks from the Yeah Yeah Yeahs’ Nick Zinner, the wispy indie-rock love god who takes up almost as much eyelash-cheekbone room as Oberst. It’s definitely weird: Both albums feature a song that takes bits of melody from the Dead Milkmen’s “Punk Rock Girl” (Digital‘s “Gold Mine Gutted” and Awake‘s “At the Bottom of Everything”), normally not a font of folk-rock inspiration. But that kind of stylistic perversity is what lets Oberst keep defying the rules. How far can he go? Stay tuned.